Objective: This study investigated the associations of adolescent cognitive ability, mental status and adaptability to school and work with unemployment from youth to mid-life. It also investigated the associations of youth unemployment with later unemployment and disability pension. Method: We used a cohort of 49 321 Swedish men, with information on cognitive ability, mental status, and school and personality characteristics in late adolescence in 1969. The information was linked to 32 years of annual administrative data to study predictors of unemployment and disability pension. Results: We found a strong and consistent association between cognitive ability and risk of unemployment, which was independent of other individual characteristics. Other notable independent risk factors were psychiatric diagnosis, contact with police or childcare authorities, smoking, risk use of alcohol, not being liked in school, and having been dismissed from or having quit a job due to unfair treatment. Unemployment before age 18 was found to be associated with unemployment across the life course, and also with disability pension, most of which was explained by individual characteristics. Conclusion: Certain individuals are more likely to be unemployed, and to be unemployed for more than one period, due to individual characteristics, which include cognitive ability, mental health, and labour-market related behaviour across the life course. However, people who become unemployed in youth have, regardless of their individual characteristics, an increased risk of becoming unemployed again. People who experience youth unemployment are also more likely to receive disability pension.